Jietacin A
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| Category | Antibiotics |
| Catalog number | BBF-01521 |
| CAS | 109766-61-2 |
| Molecular Weight | 310.47 |
| Molecular Formula | C18H34N2O2 |
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Description
Jietacin A is originally isolated from Str. sp. KP-197. It is found to be resistant to nematode, it can 100% kill Burs helenchus Lignicolus with the concentration of 0.25μg/mL, which is 10 times stronger than Avermectin B1a.
Specification
| Synonyms | Jietacine A; BRN 5538455; 1-(Ethenyl-ONN-azoxy)-14-methyl-8-pentadecanone |
| IUPAC Name | ethenyl-(14-methyl-8-oxopentadecyl)imino-oxidoazanium |
| Canonical SMILES | CC(C)CCCCCC(=O)CCCCCCCN=[N+](C=C)[O-] |
| InChI | InChI=1S/C18H34N2O2/c1-4-20(22)19-16-12-7-5-6-10-14-18(21)15-11-8-9-13-17(2)3/h4,17H,1,5-16H2,2-3H3 |
| InChI Key | BKQGCLAUQLABKR-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | parasites; fungi |
| Boiling Point | 433.1°C at 760 mmHg |
| Melting Point | 310°C |
| Density | 0.94 g/cm3 |
Reference Reading
1. Jietacins, azoxy antibiotics with potent nematocidal activity: Design, synthesis, and biological evaluation against parasitic nematodes
Akihiro Sugawara, Masahiko Kubo, Tomoyasu Hirose, Kyoichi Yahagi, Noriaki Tsunoda, Yoshihiko Noguchi, Takuji Nakashima, Yoko Takahashi, Claudia Welz, Dennis Mueller, Christina Mertens, Johannes Koebberling, Satoshi Ōmura, Toshiaki Sunazuka Eur J Med Chem. 2018 Feb 10;145:524-538. doi: 10.1016/j.ejmech.2017.12.031. Epub 2017 Dec 28.
Jietacins, an azoxy antibiotic class of chemicals, were isolated from the culture broth of Streptomyces sp. KP-197. They have a unique structural motif, including a vinyl azoxy group and a long acyclic aliphatic chain, which is usually branched but non-branched in the case of jietacin C. During a drug discovery program, we found that jietacins display potent anthelmintic activity against parasitic nematodes and that jietacin A has a moderate or low acute toxicity (LD50 > 300 mg/kg) and no mutagenic potential in a mini Ames screen. This suggests that jietacins have potential for drug discovery research. In order to create a novel anthelmintic agent, we performed design, synthesis, and biological evaluation of jietacin derivatives against parasitic nematodes. Of these derivatives, we found that a fully synthesized simplified derivative exhibited better anthelmintic activity against three parasitic nematodes than natural jietacins. In addition, it had a better efficacy in vivo through oral administration against a mouse nematode. This indicated that the azoxy motif could prove useful as a template for anthelmintic discovery, possibly creating a class of anthelmintic with novel skeletons, a potential new mode of action, and providing further insight for rational drug design.
2. Synthesis and nematocidal activities of jietacin A and its analogs
K Tsuzuki, F S Yan, K Otoguro, S Omura J Antibiot (Tokyo). 1991 Jul;44(7):774-84. doi: 10.7164/antibiotics.44.774.
Simple, efficient syntheses of jietacin A, a nematocidal antibiotic, and its analogs have been developed in order to study structure-activity relationships. A series of alpha,beta-unsaturated azoxy compounds was prepared from phenylselenomethyl azoxy compounds as key intermediates and its nematocidal activity was determined.
3. Jietacins, azoxy natural products, as novel NF-κB inhibitors: Discovery, synthesis, biological activity, and mode of action
Mariko Watanabe, Akihiro Sugawara, Yoshihiko Noguchi, Tomoyasu Hirose, Satoshi Ōmura, Toshiaki Sunazuka, Ryouichi Horie Eur J Med Chem. 2019 Sep 15;178:636-647. doi: 10.1016/j.ejmech.2019.05.079. Epub 2019 May 29.
Deregulation of NF-κB plays an important role in various diseases by controlling cell growth, inflammation, the immune response, and cytokine production. Although many NF-κB inhibitors have been developed, to the best of our knowledge, none of them have been successfully translated into clinical practice as medicines. To overcome this issue, we aimed to develop a new class of NF-κB inhibitors. Previous reports indicated that the N-terminal cysteine is a promising target for NF-κB. Based on this, we first selected 10 natural products or their derivatives from the natural product library that we developed and examined the effect on NF-κB and the viability of cancer cells with constitutively strong NF-κB activity. Among them, we found that an azoxy natural product, jietacin A, with a vinylazoxy group and an aliphatic side chain, reduced cell viability and inhibited nuclear translocation of free NF-κB. In addition, we performed design, synthesis, and biological evaluation of jietacin derivatives for development of a novel NF-κB inhibitor. Of these derivatives, a fully synthesized derivative 25 with vinylazoxy and ynone groups had a potent effect. We clarified the structure-activity relationship of this compound. Jietacin A and 25 also inhibited tumor necrosis factor-α-mediated induction of NF-κB. The NF-κB inhibitory effect depended on the N-terminal cysteine and the neighboring Arg-Ser-Ala-Gly-Ser-Ile (RSAGSI) domain of NF-κB. We also found that 25 inhibited the association between NF-κB and importin α, suggesting inhibition of NF-κB at an early step of nuclear translocation. Overall, this study indicated that the vinylazoxy motif may compose a new class of NF-κB inhibitors, providing further insight for rational drug design and rendering a unique mode of action.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
